The present invention relates to a mixture of compounds including three compounds, specifically and several other unknown compounds. The three specific known compounds in the mixture are:
(i) 2,4,6-triisobutyl-1,3,5-trioxane; having the structure: ##STR2## (ii) 2-isobutyl-4-methyl-5-ethyloxazoline and 2-isobutyl-4-ethyl-5-methyl oxazoline, each of the compounds covering by the generic formula: ##STR3## wherein R.sub.1 and R.sub.2 are different and each represents ethyl and methyl
and the use of such mixture for augmenting or enhancing the flavor or aroma of foodstuffs particularly cocoa flavored foodstuffs. The mixtures containing the three specific compounds above mentioned is prepared by admixing aqueous ammonia with isovaleraldehyde at a temperature in the range of from about 0.degree. C. up to about 10.degree. C. whereby the reaction of aqueous ammonia with isovaleraldehyde is carried out using a mole ratio of isovaleraldehyde: ammonia of from 0.5:1 up to 2:1 thereby producing an imine; then reacting the resulting imine with 2-hydroxy-3-pentanone or 3-hydroxy-2-pentanone or a mixture thereof at a temperature in the range of from about 30.degree. C. up to about 50.degree. C. over a period of time of from 1 up to 10 hours.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and aromas to (or in) foodstuffs having chocolate flavors with nutty, green and burnt, roasted flavors. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product. Thus, chocolate-like, nutty, green, burnt and roasted-like aromas and flavors are particularly desirable for many uses in foodstuff flavors, particularly chocolate flavors.
German Auslegschrift No. 2,402,416 discloses a sublimable perfumed composition in tablet form containing 1,3,5-triisopropyl-s-trioxane or 1,3,5-tri-t-butyl-s-trioxane as an active agent whereby the composition may be used to deodorize toilets, telephone mouthpieces, or give off insecticides.
2,4,6-Tri-s-butyl-1,3,5-trioxane is disclosed at volumne 19, page 391 of Beilstein; and it is further disclosed to be a "trimer" of methyl ethyl acetaldehyde (2-methyl butanal). An additional disclosure in Beilstein is at Volumn 19, supplement 2 at page 403. Neither Beilstein reference discloses the organoleptic qualities of 2,4,6-triisobutyl-1,3,5-trioxane nor is the usefulness of its presence in mixtures containing oxazolines and other materials disclosed or inferred.
Indeed, the 1,3,5-triisopropyl-s-trioxane has little, if any, aroma or flavor to be of value in flavoring foodstuffs. It is, accordingly, quite surprising that the next adjacent methyl homologue, 2,4,6-triisobutyl-1,3,5-trioxane, has such intense aroma and flavor nuances particularly when in admixture with oxazolines in the mixture of our invention.
Trialkyl substituted oxazolines are described in the prior art as being useful for modifying fish flavors in U.S. Pat. No. 3,627,540 issued on Dec. 14, 1971. More specifically, it is stated at Column 2, lines 12-27:
The seafood flavor characteristic of the pentadienal can further be varied by including one or more cyclic oxazo compounds, particularly .DELTA..sup.3 -oxazolines having the formula ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen, alkyl, or alkylene and can be the same or different. It is preferred in certain embodiments of the present invention to use lower alkyl derivatives of oxazoline, preferably those having up to about three carbon atoms in the alkyl group or groups. A preferred oxazoline in certain embodiments of the invention is 2,4,5-trimethyl-.DELTA..sup.3 -oxazoline.
U.S. Pat. No. 3,627,540 does not imply, however, that the higher alkyl oxazoline analogue of the instant invention taken together with 2,4,6-triisobutyl-1,3,5-trioxane of our invention, have flavor and aroma nuances of such quality and intensity as described herein.
Mussinan et al, "Identification and Flavor Properties of Some 3-Oxazolines and 3-Thiazolines Isolated from Cooked Beef," Abstracts of Papers, 170th Meeting, American Chemical Society, Aug. 24-29, 1975, Port City Press, Baltimore, Md., Item No. AGFD 022, stated:
22. IDENTIFICATION AND FLAVOR PROPERTIES OF SOME 3-OXAZOLINES AND 3-THIAZOLINES ISOLATED FROM COOKED BEEF. Cynthia J. Mussinan, Richard A. Wilson, Ira Katz, Anne Sanderson, and Manfred H. Vock. International Flavors and Fragrances, Inc., 1515 Highway 36, Union Beach, New Jersey 07735.
Four 3-oxazolines and two 3-thiazolines have been isolated from beef cooked in a sealed stainless steel vessel at 162.7 and 182.degree.. The compounds were identified by matching retention times and mass spectra with those of authentic compounds synthesized in our laboratory. The compounds identified were 2,4-dimethyl-3-oxazoline; 2,4,5-trimethyl-3-oxazoline; 2,4-dimethyl-5-ethyl-3-oxazoline; 2,5-dimethyl-4-ethyl-3-oxazoline; 2,4-dimethyl-3-thiazoline; and 2,4,5-trimethyl-3-thiazoline. The synthesis, spectra and flavor properties of these and some related compounds will be discussed.
None of the oxazoline compounds of Mussinan et al. have properties even remotely similar to those of the compounds containing the oxazoline moieties contained in the product-by-process of our invention. Thus, the compounds containing the oxazoline moieties included in the mixtures of our invention have aid in causing the mixtures of our invention to have unexpected, unobvious and advantageous properties with respect to their organoleptic characteristics when compared with the oxazolines of Mussinan et al. and U.S. Pat. No. 3,627,540.